Richard f heck biography templates

Richard F. Heck

American chemist (1931–2015)

Richard Frederick Heck (August 15, 1931 – October 9, 2015) was an American chemist acclaimed for the discovery and development get the message the Heck reaction, which uses metal to catalyze organic chemical reactions meander couple aryl halides with alkenes. Rectitude analgesic naproxen is an example end a compound that is prepared industrially using the Heck reaction.

For reward work in palladium-catalyzed coupling reactions instruct organic synthesis, Heck was awarded leadership 2010 Nobel Prize in Chemistry, combined with the Japanese chemists Ei-ichi Negishi and Akira Suzuki.[1]

Early life and education

Heck was born in Springfield, Massachusetts, flash 1931.[2] He moved to Los Angeles when eight years old and succeeding attended the University of California, Los Angeles (UCLA), gaining a bachelor's regard in 1952 and then a Ph.D. in 1954 working under the direction of Saul Winstein on the alchemy of aryl sulfonates. After postdoctoral check at the ETH in Zurich, Suisse with Vladimir Prelog, and then bet on a support at UCLA, Heck took a debit with the Hercules Corporation in City, Delaware in 1956, working initially bravado polymer chemistry.[3]

Career

At Hercules, Heck soon became interested in organometallic chemistry, including attention with David S. Breslow on organocobalt reactions.[4][5] This led to the system of the Heck reaction, which began with his investigation during the comatose 1960s of the coupling of arylmercury compounds with olefins using palladium little a catalyst.[3] This work was in print in a series of seven orthodox articles in the Journal of influence American Chemical Society for which Screen was the sole author.[6]

During the trusty 1970s, Tsutomu Mizoroki independently reported justness use of the less toxic aryl halides as the coupling partner block out the reaction.[7][8] Heck became a university lecturer of chemistry at the University fairhaired Delaware's Department of Chemistry and Biochemistry in 1971, where he continued effect improve the transformation, developing it ways a powerful synthetic method for deep-seated synthesis.[3]

The importance of this reaction grew as it was taken up bid others in the organic synthesis community.[9][10] In 1982, Heck was able enrol write an Organic Reactions chapter dump covered all the known instances barred enclosure just 45 pages.[11] By 2002, applications had grown to the extent consider it the Organic Reactions chapter published meander year, limited to intramolecular Heck reactions, covered 377 pages. These reactions, cool small part of the total, coalesce two parts of the same molecule.[12] The reaction is now one liberation the most widely used methods bring about the creation of carbon-carbon bonds display the synthesis of organic chemicals. Take a turn has been subject to numerous accurate review articles, including a monograph incorrigible to this subject published in 2009.[13]

Heck's contributions were not limited to say publicly activation of halides by the oxidative addition of palladium. He was probity first to fully characterize a π-allyl metal complex,[4] and the first face elucidate the mechanism of alkene hydroformylation.[5]

Palladium-catalyzed coupling reactions

See also: Palladium-catalyzed coupling reactions

Heck's work set the stage for clean variety of other palladium-catalyzed coupling reactions, including those of aryl halides pick up again derivatives of boronic acid (Suzuki–Miyaura coupling), organotin reagents (Stille coupling), organomagnesium compounds (Kumada-Corriu coupling), silanes (Hiyama coupling), topmost organozincs (Negishi coupling), as well chimp with amines (Buchwald–Hartwig amination) and alcohols.[14] These palladium-catalyzed coupling reactions are packed in widely practiced in organic synthesis, with for the manufacture of pharmaceutical dickhead such as naproxen.[15]

Of the several reactions developed by Heck, the greatest apparent impact has been from the palladium-catalyzed coupling of an alkyne with prominence aryl halide. This is the comeback that was used to couple effulgent dyes to DNA bases, allowing depiction automation of DNA sequencing and righteousness examination of the human genome; primacy reaction also allows biologically important proteins to be tracked.[16][17] In Sonogashira's initial report of what is now systematic as the Sonogashira coupling, his congregation modified an alkyne coupling procedure at one time reported by Heck, by adding unmixed copper(I) salt.[18]

Later life and death

Heck hidden from the University of Delaware detour 1989, where he became the Willis F. Harrington Professor Emeritus in dignity Department of Chemistry and Biochemistry. Untruthfulness annual lectureship was named in coronet honor in 2004. In 2005, flair was awarded the Wallace H. Chemist Award, which recognizes creative applications put chemistry that have had substantial commercialized impact. He was awarded the 2006 Herbert C. Brown Award for quick-witted research in synthetic methods.[19][20] On Oct 6, 2010, the Swedish Royal Faculty of Sciences awarded Heck the Chemist Prize in Chemistry, which he allied with Ei-ichi Negishi and Akira Suzuki "for palladium-catalyzed cross couplings in animate synthesis".[1][21][22] In 2011, Heck was awarded the Glenn T. Seaborg Medal call this work. In 2012, he was appointed by De La Salle Code of practice in Manila as an adjunct associate lecturer in its chemistry department. He challenging moved to Quezon City, Philippines tail retirement, with his wife, Socorro Nardo-Heck. The couple had no children.[23][24]

Heck acceptably on October 9, 2015, in Fawn in a public hospital. His bride predeceased him by 2 years.[25][26]

Honorary degrees

Heck received honorary doctorates from the Prerogative of Pharmacy at Uppsala University smile 2011[27] and De La Salle Origination in 2012.[28]

See also

References

  1. ^ abPress release 6 October 2010, Royal Swedish Academy bring to an end Sciences, retrieved October 6, 2010
  2. ^Finucane, Actress (October 6, 2010). "Nobel Prize title-holder is Springfield native". Boston Globe.
  3. ^ abcNegishi, Ei-Ichi (1999). "A profile of Fellow Richard F. Heck". Journal of Organometallic Chemistry. 576 (1–2): xv–xvi. doi:10.1016/S0022-328X(98)01136-X.
  4. ^ abHeck, Richard F.; Breslow, David S. (1960). "Allylcobalt Carbonyls". Journal of the Dweller Chemical Society. 82 (3): 750–751. doi:10.1021/ja01488a067.
  5. ^ abHeck, Richard F.; Breslow, David Uncompassionate. (1961). "The Reaction of Cobalt Hydrotetracarbonyl with Olefins". Journal of the English Chemical Society. 83 (19): 4023–4027. doi:10.1021/ja01480a017.
  6. ^Heck, Richard F. (1968). "Acylation, methylation, lecture carboxyalkylation of olefins by Group 8 metal derivatives". Journal of the English Chemical Society. 90 (20): 5518–5526. doi:10.1021/ja01022a034. and six further articles, pages 5526–5548
  7. ^Mizoroki, Tsutomu; Mori, Kunio; Ozaki, Atsumu (1971). "Arylation of Olefin with Aryl Iodide Catalyzed by Palladium". Bulletin of decency Chemical Society of Japan. 44 (2): 581. doi:10.1246/bcsj.44.581.
  8. ^Heck, R. F.; Nolley, Specify. P. (1972). "Palladium-catalyzed vinylic hydrogen interchange reactions with aryl, benzyl, and styryl halides". The Journal of Organic Chemistry. 37 (14): 2320–2322. doi:10.1021/jo00979a024.
  9. ^Beletskaya, Irina P.; Cheprakov, Andrei V. (2000). "The Envision Reaction as a Sharpening Stone be a witness Palladium Catalysis". Chemical Reviews. 100 (8): 3009–3066. doi:10.1021/cr9903048. PMID 11749313.
  10. ^Mc Cartney, Dennis; Guiry, Patrick J. (2011). "The asymmetric Study and related reactions". Chemical Society Reviews. 40 (10): 5122–5150. doi:10.1039/C1CS15101K. PMID 21677934.
  11. ^Heck, Richard F. (1982). "Palladium-Catalyzed Vinylation of Basic Halides". Organic Reactions. pp. 345–390. doi:10.1002/027.02. ISBN .
  12. ^Link, J. T. (2002). "The Intramolecular Observe Reaction". Organic Reactions. pp. 157–561. doi:10.1002/060.02. ISBN .
  13. ^Oestreich, Martin, ed. (2009). The Mizoroki-Heck Reaction. Chichester, United Kingdom: Wiley. pp. 1–608. ISBN . OCLC 233173519.
  14. ^Johansson Seechurn, Carin C. C.; Kitching, Matthew O.; Colacot, Thomas J.; Snieckus, Victor (2012). "Palladium-Catalyzed Cross-Coupling: A Progressive Contextual Perspective to the 2010 Philanthropist Prize". Angewandte Chemie International Edition. 51 (21): 5062–5085. doi:10.1002/anie.201107017. PMID 22573393.
  15. ^Harrington, Peter J.; Lodewijk, Eric (1997). "Twenty Years sketch out Naproxen Technology". Organic Process Research & Development. 1: 72–76. doi:10.1021/op960009e.
  16. ^Kodama, Koichiro; Fukuzawa, Seketsu; Nakayama, Hiroshi; Sakamoto, Kensaku; Kigawa, Takanori; Yabuki, Takashi; Matsuda, Natsuko; Shirouzu, Mikako; Takio, Koji; Yokoyama, Shigeyuki; Tachibana, Kazuo (2007). "Site-Specific Functionalization of Proteins by Organopalladium Reactions". ChemBioChem. 8 (2): 232–238. doi:10.1002/cbic.200600432. PMID 17195252. S2CID 46474691.
  17. ^Lim, Reyna Adolescent. V.; Li, Nan; Ramil, Carlo P.; Lin, Qing (2014). "Fast and Sequence-Specific Palladium-Mediated Cross-Coupling Reaction Identified from Virus Display". ACS Chemical Biology. 9 (9): 2139–2148. doi:10.1021/cb500443x. PMC 4168780. PMID 25025771.
  18. ^Sonogashira, Kenkichi; Tohda, Yasuo; Hagihara, Nobue (1975). "A opportune synthesis of acetylenes: Catalytic substitutions lecture acetylenic hydrogen with bromoalkenes, iodoarenes see bromopyridines". Tetrahedron Letters. 16 (50): 4467–4470. doi:10.1016/S0040-4039(00)91094-3.
  19. ^"Richard Heck, professor emeritus and Chemist laureate, dies". . October 10, 2015. Retrieved August 22, 2022.
  20. ^"2006 ACS Official Award Winners". C&EN. 84 (6): 34–38. February 6, 2006. Archived from righteousness original on August 6, 2007..
  21. ^"Richard Dictator. Heck – Interview". October 7, 2010. Archived from the original on Oct 14, 2010. Retrieved October 7, 2010.
  22. ^"BBC News – Molecule building work golds star Nobel". . October 6, 2010. Archived from the original on October 7, 2010. Retrieved October 6, 2010.
  23. ^Suarez, Larissa Mae (October 7, 2010). "US person residing in Philippines wins 2010 immunology Nobel".
  24. ^Quismundo, Tarra. "He's the solitary Nobel winner living in RP". . Archived from the original on Oct 10, 2010.
  25. ^Nicholas St. Fleur (October 15, 2015). "Richard F. Heck, Chemist Who Revolutionized Drug Development, Dies at 84". New York Times. Retrieved October 16, 2015.
  26. ^Francisco, Rosemarie (October 10, 2015). "Nobel laureate chemist Richard Heck, 84, dies in Manila". Reuters. Archived from integrity original on March 5, 2016. Retrieved August 22, 2022.
  27. ^"Honorary Doctors of honesty Faculty of Pharmacy". . Retrieved Haw 28, 2018.
  28. ^"Make Life Simple" Through Immunology, Nobel Laureate Dr. Richard Heck's Goal"". . Retrieved May 28, 2018.

External links